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Olivia Rodrigo called up her former tour opener Chappell Roan to help remix “Expectations,” one of the standout songs on her new album, You Seem Pretty Sad for a Girl So in Love. Even better, the two pop stars went all-in for its music video, in which they join a gameshow hosted by noted Rodrigo fan David Byrne. Rodrigo and Roan’s producer Dan Nigro also makes a special appearance. Watch the video below.
Rodrigo is currently on the Unraveled Tour in support of You Seem Pretty Sad for a Girl So in Love. Her third studio album follows 2023’s Guts and marks even bigger ambitions, both musically with songs like “The Cure,” “Serena Joy,” and her Robert Smith duet “What’s Wrong With Me,” and externally with her live performances, having organized the inaugural charity music festival Daisy Chain Fields with an all-star lineup celebrating womanhood. Read about how it all came together in Shaad D’Souza’s Pitchfork cover story, Olivia Rodrigo: Blood on the Tracks.
Roan released her debut album, The Rise and Fall of a Midwest Princess, in 2023 after a long, winding path as a songwriter leading up to then. The following year, Roan rapidly ascended in popularity, thanks in large part to her live sets opening for Rodrigo and viral music festival performances. After taking home Best New Artist at the 2025 Grammy Awards, she dropped “The Giver,” her first new single since her LP, and then months later followed it with “The Subway,” which earned her two Grammy nominations at this year’s ceremony. Next week, she’ll host a charity show, The Super Graphic Spectacular, with performances slotted from Caroline Polachek, Tinashe, MUNA, and more.
Read about Guts and The Rise and Fall of a Midwest Princess in The Best Pop Music of 2023.